Abstract
We have found a novel metabolic pathway of phenols catalyzed by cytochrome P450 and its chemical models. When various p-substituted phenols (substituent = OPh, NO2, CN, CH2OH, COCH3, COPh, COOH, F, Cl, and Br) were reacted with rat liver microsomes system or meso-tetraphenylporphinatoiron(III) chloride model system, the substituent was eliminated to produce hydroquinone. In the case of p-cresol, p-toluquinol was formed instead of hydroquinone. To elucidate how the substituent is eliminated, we attempted to detect the product derived from the eliminated group. Results indicated that the mechanism of this reaction can be divided into two types: the substituent is eliminated as an anion and as a cation. P450 also catalyzed phenol coupling reaction to give biphenyl derivatives, diphenyl ether derivatives, and dibenzodioxin.
| Original language | English |
|---|---|
| Pages (from-to) | 1202-1209 |
| Number of pages | 8 |
| Journal | Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry |
| Volume | 58 |
| Issue number | 12 |
| Publication status | Published - 2000 Dec |
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Keywords
- Cytochrome P450
- Cytochrome P450 model
- Dibenzodioxin
- Drug metabolism
- Estrogen
- Phenol coupling
- Phenol metabolism
ASJC Scopus subject areas
- Organic Chemistry
Cite this
Novel metabolic pathway of phenols catalyzed by cytochrome P450 and its mechanism. / Mashino, Tadahiko.
In: Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, Vol. 58, No. 12, 12.2000, p. 1202-1209.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Novel metabolic pathway of phenols catalyzed by cytochrome P450 and its mechanism
AU - Mashino, Tadahiko
PY - 2000/12
Y1 - 2000/12
N2 - We have found a novel metabolic pathway of phenols catalyzed by cytochrome P450 and its chemical models. When various p-substituted phenols (substituent = OPh, NO2, CN, CH2OH, COCH3, COPh, COOH, F, Cl, and Br) were reacted with rat liver microsomes system or meso-tetraphenylporphinatoiron(III) chloride model system, the substituent was eliminated to produce hydroquinone. In the case of p-cresol, p-toluquinol was formed instead of hydroquinone. To elucidate how the substituent is eliminated, we attempted to detect the product derived from the eliminated group. Results indicated that the mechanism of this reaction can be divided into two types: the substituent is eliminated as an anion and as a cation. P450 also catalyzed phenol coupling reaction to give biphenyl derivatives, diphenyl ether derivatives, and dibenzodioxin.
AB - We have found a novel metabolic pathway of phenols catalyzed by cytochrome P450 and its chemical models. When various p-substituted phenols (substituent = OPh, NO2, CN, CH2OH, COCH3, COPh, COOH, F, Cl, and Br) were reacted with rat liver microsomes system or meso-tetraphenylporphinatoiron(III) chloride model system, the substituent was eliminated to produce hydroquinone. In the case of p-cresol, p-toluquinol was formed instead of hydroquinone. To elucidate how the substituent is eliminated, we attempted to detect the product derived from the eliminated group. Results indicated that the mechanism of this reaction can be divided into two types: the substituent is eliminated as an anion and as a cation. P450 also catalyzed phenol coupling reaction to give biphenyl derivatives, diphenyl ether derivatives, and dibenzodioxin.
KW - Cytochrome P450
KW - Cytochrome P450 model
KW - Dibenzodioxin
KW - Drug metabolism
KW - Estrogen
KW - Phenol coupling
KW - Phenol metabolism
UR - http://www.scopus.com/inward/record.url?scp=21144437856&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=21144437856&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:21144437856
VL - 58
SP - 1202
EP - 1209
JO - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
JF - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
SN - 0037-9980
IS - 12
ER -